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Organic Chemistry Is Awesome
Over 300+ blog posts to guide you through introductory Organic Chemistry, organized by subject.
00 General Chemistry Review
- From Gen Chem to Organic Chem, Part 14: Wrapup
- From Gen Chem to Organic Chem, Pt. 13 - Equilibria
- From Gen Chem to Org Chem Pt. 12 - Kinetics
- From Gen Chem to Organic Chem, Pt. 11 - The Second Law
- From Gen Chem to Organic Chem, Pt. 10 - Hess' Law
- From Gen Chem to Org Chem, Pt. 9 - Acids and Bases
- From Gen Chem to Org Chem, Pt. 8 - Ionic and Covalent Bonding
- From Gen Chem to Org Chem, Pt. 7 - Lewis Structures
- From Gen Chem to Org Chem, Pt. 6 - Lewis Structures, A Parable
- From Gen Chem to Organic Chem, Pt. 5 - Understanding Periodic Trends
- From Gen Chem to Organic Chem, Pt. 4 - Chemical Bonding
- From Gen Chem to Organic Chem, Pt. 3 - Effective Nuclear Charge
- From Gen Chem to Organic Chem, Pt. 2 - Electrons and Orbitals
- How Gen Chem Relates to Organic Chem, Pt. 1 - The Atom
- Gen Chem and Organic Chem: How are they different?
01 Bonding, Structure, and Resonance
- Orbital Hybridization And Bond Strengths
- How To Determine Hybridization: A Shortcut
- Hybrid Orbitals
- How Do We Know Methane (CH4) Is Tetrahedral?
- Review of Atomic Orbitals for Organic Chemistry
- How Concepts Build Up In Org 1 ("The Pyramid")
- How to apply electronegativity and resonance to understand reactivity
- Drawing Resonance Structures: 3 Common Mistakes To Avoid
- In Summary: Evaluating Resonance Structures
- Exploring Resonance: Pi-acceptors
- Exploring Resonance: Pi-Donation
- Evaluating Resonance Structures With Positive Charge
- Evaluating Resonance Structures With Negative Charges
- How To Find The Best Resonance Structure By Applying Electronegativity
- Evaluating Resonance Forms (1) - The Rule of Least Charges
- How To Use Curved Arrows To Interchange Resonance Forms
- Introduction to Resonance
- How To Use Electronegativity To Determine Electron Density (and why NOT to trust formal charge)
- Partial Charges Give Clues About Electron Flow
- 3 Trends That Affect Boiling Points
- Sigma bonds come in six varieties: Pi bonds come in one
- The Four Intermolecular Forces and How They Affect Boiling Points
- A Key Skill: How to Calculate Formal Charge
02 Acid Base Reactions
- pKa Values Span 60 Orders Of Magnitude
- How Protonation and Deprotonation Affect Reactivity
- Acid Base Reactions Are Fast
- A Handy Rule of Thumb for Acid-Base Reactions
- Acid-Base Reactions: Introducing Ka and pKa
- Walkthrough of Acid-Base Reactions (3) - Acidity Trends
- The Stronger The Acid, The Weaker The Conjugate Base
- Acid Base Reactions In Organic Chemistry
- Introduction to Acid-Base Reactions
- How to Use a pKa Table
- Five Key Factors That Influence Acidity
- The pKa Table Is Your Friend
03 Alkanes and Nomenclature
- Organic Chemistry IUPAC Nomenclature Demystified With A Simple Puzzle Piece Approach
- Common Mistakes: Drawing Tetrahedral Carbons
- Don't Be Futyl, Learn The Butyls
- Hidden Hydrogens, Hidden Lone Pairs, Hidden Counterions
- Condensed Formulas: Deciphering What the Brackets Mean
- Table of Functional Group Priorities for Nomenclature
- Summary Sheet - Alkane Nomenclature
- The Many, Many Ways of Drawing Butane
- Meet the (Most Important) Functional Groups
- Common Mistakes in Organic Chemistry: Pentavalent Carbon
- Branching, and Its Affect On Melting and Boiling Points
- Primary, Secondary, Tertiary, Quaternary In Organic Chemistry
04 Conformations and Cycloalkanes
- Putting the Newman into ACTION
- Newman Projections
- Bredt's Rule (And Summary of Cycloalkanes)
- Naming Bicyclic Compounds - Fused, Bridged, and Spiro
- Fused Rings - Cis-Decalin and Trans-Decalin
- Cyclohexane Chair Conformation Stability: Which One Is Lower Energy?
- Ranking The Bulkiness Of Substituents On Cyclohexanes: "A-Values"
- Substituted Cyclohexanes - Axial vs Equatorial
- The Cyclohexane Chair Flip - Energy Diagram
- The Cyclohexane Chair Flip
- How To Draw The Cyclohexane Chair Conformation
- Cyclohexane Chair Conformation: An Aerial Tour
- Cyclohexane Conformations
- Cycloalkanes - Ring Strain In Cyclopropane And Cyclobutane
- Calculation of Ring Strain In Cycloalkanes
- Geometric Isomers In Small Rings: Cis And Trans Cycloalkanes
- Introduction to Cycloalkanes (1)
- The Ups and Downs of Cyclohexanes
05 A Primer On Organic Reactions
- Learning Organic Chemistry Reactions: A Checklist (PDF)
- Leaving Groups Are Nucleophiles Acting In Reverse
- What Makes A Good Nucleophile?
- Nucleophilicity vs. Basicity
- Nucleophiles and Electrophiles
- 7 Factors That Stabilize Positive Charge in Organic Chemistry
- Curved Arrows (2): Initial Tails and Final Heads
- 7 Factors that stabilize negative charge in organic chemistry
- Common Mistakes: Formal Charges Can Mislead
- The Third Most Important Question to Ask When Learning A New Reaction
- Curved Arrows (for reactions)
- Learning New Reactions: How Do The Electrons Move?
- Introduction to Oxidative Cleavage Reactions
- Introduction to Free Radical Substitution Reactions
- Introduction to Elimination Reactions
- Grossman's Rule
- Introduction to Addition Reactions
- Hammond's Postulate
- The 4 Major Classes of Reactions in Org 1
- The Most Important Question To Ask When Learning a New Reaction
- How (and why) electrons flow
- Draw The Ugly Version First
- What makes a good leaving group?
- Three Factors that Destabilize Carbocations
- 3 Factors That Stabilize Carbocations
- The Three Classes of Nucleophiles
- What's a Transition State?
06 Free Radical Reactions
- Synthesis (2) - Reactions of Alkanes
- In Summary: Free Radicals
- Bonus Topic: Allylic Rearrangements
- Allylic Bromination
- Halogenation At Tiffany's
- Selectivity in Free Radical Reactions: Bromination vs. Chlorination
- Selectivity In Free Radical Reactions
- Monochlorination Products Of Propane, Pentane, And Other Alkanes
- Initiation, Propagation, Termination
- Free Radical Initiation: Why Is "Light" Or "Heat" Required?
- Bond Strengths And Radical Stability
- What Factors Destabilize Free Radicals?
- 3 Factors That Stabilize Free Radicals
- Free Radical Reactions
- Bond Dissociation Energies = Homolytic Cleavage
07 Stereochemistry and Chirality
- How To Determine R and S Configurations On A Fischer Projection
- Enantiomers vs Diastereomers vs The Same? Two Methods For Solving Problems
- Types of Isomers: Constitutional Isomers, Stereoisomers, Enantiomers, and Diastereomers
- Optical Purity and Enantiomeric Excess
- Optical Rotation, Optical Activity, and Specific Rotation
- Assigning R/S To Newman Projections (And Converting Newman To Line Diagrams)
- Assigning Cahn-Ingold-Prelog (CIP) Priorities (2) - The Method of Dots
- Introduction to Assigning (R) and (S): The Cahn-Ingold-Prelog Rules
- Chiral Allenes And Chiral Axes
- What's a Racemic Mixture?
- The Single Swap Rule
- The Meso Trap
- On Cats, Part 6: Stereocenters
- On Cats, Part 4: Enantiocats
08 Substitution Reactions
- Comparing the SN1 and SN2 Reactions
- The Conjugate Acid Is A Better Leaving Group
- The SN1 Mechanism
- Why the SN2 Reaction Is Powerful
- The SN2 Mechanism
- Two Types of Nucleophilic Substitution Reactions
- Walkthrough of Substitution Reactions (1) - Introduction
- Polar Protic? Polar Aprotic? Nonpolar? All About Solvents
- Introduction to Nucleophilic Substitution Reactions
- Steric Hindrance is Like a Fat Goalie
- Common Blind Spot: Intramolecular Reactions
- The Conjugate Base is Always a Stronger Nucleophile
09 Elimination Reactions
- Elimination (E1) Reactions With Rearrangements
- Comparing the E1 vs SN1 Reactions
- Bulky Bases in Elimination Reactions
- Antiperiplanar Relationships: The E2 Reaction and Cyclohexane Rings
- E1 vs E2: Comparing the E1 and E2 Reactions
- The E2 Mechanism
- The E1 Reaction
- Two Elimination Reaction Patterns
- Elimination Reactions Are Favored By Heat
- Elimination Reactions (2): The Zaitsev Rule
- Elimination Reactions (1): Introduction And The Key Pattern
11 SN1/SN2/E1/E2 Decision
12 Alkene Reactions
- E and Z Notation For Alkenes (+ Cis/Trans)
- Synthesis (4) - Alkene Reaction Map, Including Alkyl Halide Reactions
- Summary: Three Key Families Of Alkene Reaction Mechanisms
- Alkene Reactions: Ozonolysis
- A Fourth Alkene Addition Pattern - Free Radical Addition
- Bromonium Ion Formation: A (Minor) Arrow-Pushing Dilemma
- Alkene Addition Pattern #3: The "Concerted" Pathway
- Hydroboration Oxidation of Alkenes Mechanism
- Hydroboration - Oxidation of Alkenes
- Alkene Addition Pattern #2: The "Three-Membered Ring" Pathway
- Bromination of Alkenes: The Mechanism
- Bromination of Alkenes
- Rearrangements in Alkene Addition Reactions
- Addition Pattern #1: The "Carbocation Pathway"
- Arrow Pushing and Alkene Addition Reactions
- Alkene Hydrohalogenation Mechanism And How It Explains Markovnikov's Rule
- Markovnikov Addition Of HCl To Alkenes
- Stereoselectivity In Alkene Addition Reactions: Syn vs Anti Addition
- Regioselectivity In Alkene Addition Reactions
- Addition Reactions: Elimination's Opposite
- Selective vs. Specific
13 Alkyne Reactions
- Synthesis (5) - Reactions of Alkynes
- Alkynes Are A Blank Canvas
- Alkenes To Alkynes Via Halogenation And Elimination Reactions
- Alkyne Reactions - The "Concerted" Pathway
- Alkyne Halogenation: Bromination, Chlorination, and Iodination of Alkynes
- Alkyne Reaction Patterns - Hydrohalogenation - Carbocation Pathway
- Hydroboration and Oxymercuration of Alkynes
- Partial Reduction of Alkynes To Obtain Cis or Trans Alkenes
- Acetylides from Alkynes, And Substitution Reactions of Acetylides
14 Alcohols, Epoxides and Ethers
- Alcohol Reactions Roadmap (PDF)
- Thiols And Thioethers
- Protecting Groups For Alcohols
- Intramolecular Reactions of Alcohols and Ethers
- Demystifying Alcohol Oxidations
- Alcohol Oxidation: "Strong" and "Weak" Oxidants
- Elimination of Alcohols To Alkenes With POCl3
- Elimination Reactions of Alcohols
- PBr3 and SOCl2
- Tosylates And Mesylates
- Making Alkyl Halides From Alcohols
- Epoxide Ring Opening With Base
- Opening of Epoxides With Acid
- Epoxides - The Outlier Of The Ether Family
- Cleavage Of Ethers With Acid
- Alcohols To Ethers via Acid Catalysis
- Ethers From Alkenes, Tertiary Alkyl Halides and Alkoxymercuration
- Williamson Ether Synthesis: Planning
- The Williamson Ether Synthesis
- Alcohols (3) - Acidity and Basicity
- Alcohols Can Act As Acids Or Bases (And Why It Matters)
- Alcohols (1) - Nomenclature and Properties
- SOCl2 Mechanism For Alcohols To Alkyl Halides: SN2 versus SNi
- Oxidation Ladders
- Oxidation and Reduction in Organic Chemistry
- Calculating the oxidation state of a carbon
- Reaction Map: Reactions of Organometallics
- The Heck, Suzuki, and Olefin Metathesis Reactions (And Why They Don't Belong In Most Introductory Organic Chemistry Courses)
- Gilman Reagents (Organocuprates): What They're Used For
- Organocuprates (Gilman Reagents): How They're Made
- Grignard Reactions And Synthesis (2)
- Grignard Practice Problems: Synthesis (1)
- Protecting Groups In Grignard Reactions
- Reactions of Grignard Reagents
- Organometallics Are Strong Bases
- Formation of Grignard and Organolithium Reagents
- What's An Organometallic?
- Common Mistakes with Carbonyls: Carboxylic Acids... Are Acids!
- IR Spectroscopy: 4 Practice Problems
- Infrared Spectroscopy: A Quick Primer On Interpreting Spectra
- Bond Vibrations, Infrared Spectroscopy, and the "Ball and Spring" Model
- UV-Vis Spectroscopy: Practice Questions
- UV-Vis Spectroscopy: Absorbance of Carbonyls
- Introduction To UV-Vis Spectroscopy
- Conjugation And Color (+ How Bleach Works)
- Degrees of Unsaturation (or IHD, Index of Hydrogen Deficiency)
- Structure Determination Case Study: Deer Tarsal Gland Pheromone
- Natural Product Isolation (2) - Purification Techniques, An Overview
- Natural Product Isolation (1) - Extraction
- Liquid Gold: Pheromones In Doe Urine
- Homotopic, Enantiotopic, Diastereotopic
17 Dienes and MO Theory
- The Intramolecular Diels Alder Reaction
- The Cope and Claisen Rearrangements
- Regiochemistry In The Diels-Alder Reaction
- The Retro Diels-Alder Reaction
- Diels-Alder Reaction: Kinetic and Thermodynamic Control
- Why Are Endo vs Exo Products Favored in the Diels-Alder Reaction?
- HOMO and LUMO In the Diels Alder Reaction
- Exo vs Endo Products In The Diels Alder: How To Tell Them Apart
- Stereochemistry of the Diels-Alder Reaction
- Cyclic Dienes and Dienophiles in the Diels-Alder Reaction
- The Diels-Alder Reaction
- s-cis and s-trans
- More On 1,2 and 1,4 Additions To Dienes
- Reactions of Dienes: 1,2 and 1,4 Addition
- Pi Molecular Orbitals of Butadiene
- Molecular Orbitals of The Allyl Cation, Allyl Radical, and Allyl Anion
- Bonding And Antibonding Pi Orbitals
- Conjugation And Resonance In Organic Chemistry
- How Concepts Build Up In Org 2
- Thermodynamic and Kinetic Products
- Are these molecules conjugated?
- What To Expect In Organic Chemistry 2
19 Reactions of Aromatic Molecules
- Birch Reduction
- Aromatic Synthesis (3) - Sulfonyl Blocking Groups
- Synthesis (7): Reaction Map of Benzene and Related Aromatic Compounds
- Synthesis of Benzene Derivatives (2) - Polarity Reversal
- Aromatic Synthesis (1) - "Order Of Operations"
- More Reactions on the Aromatic Sidechain: Reduction of Nitro Groups and the Baeyer Villiger
- Nucleophilic Aromatic Substitution (2) - The Benzyne Mechanism
- The Wolff-Kishner, Clemmensen, And Other Carbonyl Reductions
- Nucleophilic Aromatic Substitution (NAS)
- Reactions on the "Benzylic" Carbon: Bromination And Oxidation
- Intramolecular Friedel-Crafts Reactions
- EAS Reactions (3) - Friedel-Crafts Acylation and Friedel-Crafts Alkylation
- Electrophilic Aromatic Substitutions (2) - Nitration and Sulfonation
- Electrophilic Aromatic Substitutions (1) - Halogenation of Benzene
- Disubstituted Benzenes: The Strongest Electron-Donor "Wins"
- Why are halogens ortho- para- directors?
- Understanding Ortho, Para, and Meta Directors
- Ortho-, Para- and Meta- Directors in Electrophilic Aromatic Substitution
- Electrophilic Aromatic Substitution - The Mechanism
- Activating and Deactivating Groups In Electrophilic Aromatic Substitution
- Electrophilic Aromatic Substitution: Introduction
20 Aldehydes and Ketones
- Wittig Reaction
- Aldehydes and Ketones: 14 Reactions With The Same Mechanism
- What's The Alpha Carbon In Carbonyl Compounds?
- On Acetals and Hemiacetals
- Imines and Enamines
- Acid Catalysis Of Carbonyl Addition Reactions: Too Much Of A Good Thing?
- Breaking Down Carbonyl Reaction Mechanisms: Reactions of Anionic Nucleophiles (Part 2)
- Breaking Down Carbonyl Reaction Mechanisms: Anionic Nucleophiles (Part 1)
- Carbonyls: 10 key concepts (Part 2)
- Carbonyl Chemistry: 10 Key Concepts (Part 1)
21 Carboxylic Acid Derivatives
- Amide Hydrolysis
- Making Music With Mechanisms (PADPED)
- Simplifying the reactions of carboxylic acid derivatives (part 1)
- Summary Sheet #7 - 21 Carbonyl Mechanisms on 1 page
- Carbonyl Chemistry: Learn Six Mechanisms For the Price Of One
- Carbonyl chemistry: Anionic versus Neutral Nucleophiles
- Summary Sheet #5 - 9 Key Mechanisms in Carbonyl Chemistry
- How Reactions Are Like Music
- Let's Talk About the [1,2] Elimination
- Proton Transfers Can Be Tricky
- Carbonyl Mechanisms: Neutral Nucleophiles, Part 1
- The Magic Wand of Proton Transfer
- The Power of Acid Catalysis
22 Enols and Enolates
- Introduction to Peptide Synthesis
- Reactions of Diazonium Salts: Sandmeyer and Related Reactions
- The Strecker Synthesis of Amino Acids
- The Cope Elimination
- Some Reactions of Azides
- Protecting Groups for Amines - Carbamates
- Nucleophilicity of Amines
- The Amide Functional Group: Properties, Synthesis, and Nomenclature
- The Gabriel Synthesis
- The Hofmann Elimination
- The Hofmann and Curtius Rearrangements
- Reductive Amination
- Alkylation of Amines (Sucks!)
- The Mesomeric Effect And Aromatic Amines
- 5 Key Basicity Trends of Amines
- Basicity of Amines And pKaH
- The Ruff Degradation and Kiliani-Fischer Synthesis
- Reactions of Sugars: Glycosylation and Protection
- The Big Damn Post Of Carbohydrate-Related Chemistry Definitions
- Converting a Fischer Projection To A Haworth (And Vice Versa)
- The Haworth Projection
- Reducing Sugars
- What is Mutarotation?
- Pyranoses and Furanoses: Ring-Chain Tautomerism In Sugars
- D and L Notation For Sugars
25 Fun and Miscellaneous
- Organic Chemistry and the New MCAT
- A Gallery of Some Interesting Molecules From Nature
- The Organic Chemistry Behind "The Pill"
- Maybe they should call them, "Formal Wins" ?
- Planning Organic Synthesis With "Reaction Maps"
- Organic Chemistry Is Shit
- The 8 Types of Arrows In Organic Chemistry, Explained
- The Most Annoying Exceptions in Org 1 (Part 2)
- The Most Annoying Exceptions in Org 1 (Part 1)
- On Cats, Part 2: Cat Line Diagrams
- On Cats, Part 1: Conformations and Configurations
- Screw Organic Chemistry, I'm Just Going To Write About Cats
- The Marriage May Be Bad, But the Divorce Still Costs Money
- Why Do Organic Chemists Use Kilocalories?
- What Holds The Nucleus Together?
- 9 Nomenclature Conventions To Know
Always Rigorous...Molecular Orbital Interactions In Diels-Alder Reactions
Often Irreverent...How Do We Know Methane Is Tetrahedral?
Occasionally ProfaneOrganic Chemistry Is Shit
Case Studies Of Successful Students
Last semester I had the pleasure of working with “Chris” (a pseudonym) on second-semester organic chemistry topics. Before we met, Chris had already obtained a
How Helena Got 93 In Organic Chemistry An Australian reader, Helena, recently wrote to say she’d earned a 93 in her organic chemistry class as
From The Blog
Founder, Master Organic Chemistry
After doing a Ph. D. in organic synthesis at McGill and a postdoc at MIT, I applied for faculty positions at universities during the Great Recession. It didn’t work out. But having seen first-hand how many people struggled with the subject (including myself when I took it as an undergraduate) I thought there was a need for an online organic chemistry resource that had all the rigor of a traditional textbook, but was more approachable and accessible.
Drawing on the experience of thousands of hours spent tutoring students 1-on-1, as well as dozens of case studies, Master Organic Chemistry aims to fill in some of the conceptual gaps that aren’t traditionally covered by textbooks, and provide a friendly, logical and thorough pathway for learning introductory organic chemistry.